(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one → HCID 58109311, compound

HRID 2037482Notes

Reaction equation

HRID 2037482 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][CH2:23][CH2:24][OH:25])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:25][CH2:24][CH2:23][CH2:22][C@@:13]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:12][C:11](=[O:26])[N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:11]([O:12][CH3:13])=[O:26])=[CH:3][CH:4]=2)[CH3:9])[CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 59532368(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 58109311HCID 58109311, compoundYield 158.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (80 mg, 0.19 mmol), Pd(PPh3)2Cl2 (14 mg, 0.02 mmol) and TEA (38 mg, 0.38 mmol) in methanol (10 mL) was stirred in a sealed tube under 50 Psi carbon monoxide atmosphere at 80° C. overnight. The mixture was filtered, and the filtrate was concentrated to give the crude product, which was purified by preparative TLC to give methyl 4-((S)-1-((R)-6-(3-hydroxypropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)benzoate (60 mg, crude).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-33890dcebd044044b5e75529a4c5f06c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…